ES2291882T3 - Derivados de 2-(6-amino-piridin-3-il)-2-hidroxietilamina como agonistas de adrenoceptores beta 2. - Google Patents

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Publication number

ES2291882T3

ES2291882T3 ES04735621T ES04735621T ES2291882T3 ES 2291882 T3 ES2291882 T3 ES 2291882T3 ES 04735621 T ES04735621 T ES 04735621T ES 04735621 T ES04735621 T ES 04735621T ES 2291882 T3 ES2291882 T3 ES 2291882T3

Authority

ES

Spain

Prior art keywords

propyl

amino

hydroxy

phenyl

aminopyridin

Prior art date

2003-06-04

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Lifetime

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• 239000000556 agonist Substances 0.000 title claims description 21
• 108060003345 Adrenergic Receptor Proteins 0.000 title claims description 8
• 102000017910 Adrenergic receptor Human genes 0.000 title claims description 8
• -1 SR9 Chemical group 0.000 claims abstract description 454
• 150000001875 compounds Chemical class 0.000 claims abstract description 285
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 109
• 150000003839 salts Chemical class 0.000 claims abstract description 38
• 239000012453 solvate Substances 0.000 claims abstract description 14
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
• 230000000155 isotopic effect Effects 0.000 claims abstract description 8
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 5
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 3
• 125000003386 piperidinyl group Chemical group 0.000 claims abstract description 3
• 125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims abstract description 3
• 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims abstract description 3
• 125000001475 halogen functional group Chemical group 0.000 claims abstract 3
• 238000002360 preparation method Methods 0.000 claims description 273
• 239000000203 mixture Substances 0.000 claims description 82
• 239000002253 acid Substances 0.000 claims description 74
• 150000001412 amines Chemical class 0.000 claims description 67
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 50
• 208000006673 asthma Diseases 0.000 claims description 42
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 34
• 125000000217 alkyl group Chemical group 0.000 claims description 31
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 30
• 239000003814 drug Substances 0.000 claims description 29
• 206010006451 bronchitis Diseases 0.000 claims description 27
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 26
• 201000010099 disease Diseases 0.000 claims description 26
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 26
• 238000011282 treatment Methods 0.000 claims description 26
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 20
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
• 201000009267 bronchiectasis Diseases 0.000 claims description 18
• 239000003795 chemical substances by application Substances 0.000 claims description 15
• 229940079593 drug Drugs 0.000 claims description 15
• 102000016966 beta-2 Adrenergic Receptors Human genes 0.000 claims description 11
• 108010014499 beta-2 Adrenergic Receptors Proteins 0.000 claims description 11
• 229910052801 chlorine Inorganic materials 0.000 claims description 11
• 229910052731 fluorine Inorganic materials 0.000 claims description 11
• 229910052739 hydrogen Inorganic materials 0.000 claims description 11
• 150000003930 2-aminopyridines Chemical class 0.000 claims description 10
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 10
• 239000005557 antagonist Substances 0.000 claims description 10
• 239000003112 inhibitor Substances 0.000 claims description 10
• 125000006239 protecting group Chemical group 0.000 claims description 10
• MODKMHXGCGKTLE-UHFFFAOYSA-N N-acetyl-beta-phenethylamine Natural products CC(=O)NCCC1=CC=CC=C1 MODKMHXGCGKTLE-UHFFFAOYSA-N 0.000 claims description 9
• 230000000172 allergic effect Effects 0.000 claims description 9
• 208000010668 atopic eczema Diseases 0.000 claims description 9
• 230000001404 mediated effect Effects 0.000 claims description 9
• 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 8
• 208000035475 disorder Diseases 0.000 claims description 8
• 230000008506 pathogenesis Effects 0.000 claims description 8
• 102000005962 receptors Human genes 0.000 claims description 8
• 108020003175 receptors Proteins 0.000 claims description 8
• 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims description 7
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
• 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 6
• 125000006185 3,4-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C(=C1[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])* 0.000 claims description 6
• 102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 claims description 6
• 108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 claims description 6
• 208000024711 extrinsic asthma Diseases 0.000 claims description 6
• 239000003862 glucocorticoid Substances 0.000 claims description 6
• 239000003199 leukotriene receptor blocking agent Substances 0.000 claims description 6
• 229940037128 systemic glucocorticoids Drugs 0.000 claims description 6
• ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 claims description 6
• 206010006482 Bronchospasm Diseases 0.000 claims description 5
• 230000007885 bronchoconstriction Effects 0.000 claims description 5
• 230000002757 inflammatory effect Effects 0.000 claims description 5
• 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 5
• 230000000414 obstructive effect Effects 0.000 claims description 5
• 210000002345 respiratory system Anatomy 0.000 claims description 5
• 206010006458 Bronchitis chronic Diseases 0.000 claims description 4
• 206010014561 Emphysema Diseases 0.000 claims description 4
• 230000003213 activating effect Effects 0.000 claims description 4
• 230000001154 acute effect Effects 0.000 claims description 4
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
• VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 4
• 208000015181 infectious disease Diseases 0.000 claims description 4
• 230000002458 infectious effect Effects 0.000 claims description 4
• 201000010659 intrinsic asthma Diseases 0.000 claims description 4
• 208000011580 syndromic disease Diseases 0.000 claims description 4
• FTFZJGUKLJRXDO-JPYJTQIMSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-benzylacetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1CC(=O)NCC1=CC=CC=C1 FTFZJGUKLJRXDO-JPYJTQIMSA-N 0.000 claims description 3
• 101150051188 Adora2a gene Proteins 0.000 claims description 3
• 208000000884 Airway Obstruction Diseases 0.000 claims description 3
• 239000000812 cholinergic antagonist Substances 0.000 claims description 3
• 208000007451 chronic bronchitis Diseases 0.000 claims description 3
• 230000001684 chronic effect Effects 0.000 claims description 3
• 230000008878 coupling Effects 0.000 claims description 3
• 238000010168 coupling process Methods 0.000 claims description 3
• 238000005859 coupling reaction Methods 0.000 claims description 3
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 239000008194 pharmaceutical composition Substances 0.000 claims description 3
• 239000003379 purinergic P1 receptor agonist Substances 0.000 claims description 3
• 229960000278 theophylline Drugs 0.000 claims description 3
• UUIIWUKNVUTSNE-ZHRRBRCNSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-(3-hydroxy-4-methoxyphenyl)acetamide Chemical compound C1=C(O)C(OC)=CC=C1NC(=O)CC1=CC=CC(C[C@@H](C)NC[C@H](O)C=2C=NC(N)=CC=2)=C1 UUIIWUKNVUTSNE-ZHRRBRCNSA-N 0.000 claims description 2
• IGKRIIXFWGRSBG-ZHRRBRCNSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-(4-hydroxyphenyl)acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1CC(=O)NC1=CC=C(O)C=C1 IGKRIIXFWGRSBG-ZHRRBRCNSA-N 0.000 claims description 2
• DEBJXINLCPCOPT-ZNSGIYGDSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-(5-hydroxy-1,2,3,4-tetrahydronaphthalen-1-yl)acetamide Chemical compound C1([C@@H](O)CN[C@@H](CC=2C=C(CC(=O)NC3C4=CC=CC(O)=C4CCC3)C=CC=2)C)=CC=C(N)N=C1 DEBJXINLCPCOPT-ZNSGIYGDSA-N 0.000 claims description 2
• RSNFSUNKQNRTED-CJAUYULYSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-(5-tert-butyl-2-hydroxyphenyl)acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1CC(=O)NC1=CC(C(C)(C)C)=CC=C1O RSNFSUNKQNRTED-CJAUYULYSA-N 0.000 claims description 2
• BOBQZGKXKNTVCI-CLOONOSVSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[2-(3-ethoxy-4-hydroxyphenyl)ethyl]acetamide Chemical compound C1=C(O)C(OCC)=CC(CCNC(=O)CC=2C=C(C[C@@H](C)NC[C@H](O)C=3C=NC(N)=CC=3)C=CC=2)=C1 BOBQZGKXKNTVCI-CLOONOSVSA-N 0.000 claims description 2
• YSWKWILLLWJXAR-KOSHJBKYSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[2-(3-hydroxy-4-methoxyphenyl)ethyl]acetamide Chemical compound C1=C(O)C(OC)=CC=C1CCNC(=O)CC1=CC=CC(C[C@@H](C)NC[C@H](O)C=2C=NC(N)=CC=2)=C1 YSWKWILLLWJXAR-KOSHJBKYSA-N 0.000 claims description 2
• CFMCVVNBOUEDMY-KOSHJBKYSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[2-(4-hydroxy-3-methoxyphenyl)ethyl]acetamide Chemical compound C1=C(O)C(OC)=CC(CCNC(=O)CC=2C=C(C[C@@H](C)NC[C@H](O)C=3C=NC(N)=CC=3)C=CC=2)=C1 CFMCVVNBOUEDMY-KOSHJBKYSA-N 0.000 claims description 2
• NDFUIKXWIDLZFV-KOSHJBKYSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[2-(4-hydroxyphenyl)ethyl]acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1CC(=O)NCCC1=CC=C(O)C=C1 NDFUIKXWIDLZFV-KOSHJBKYSA-N 0.000 claims description 2
• MQIBAVICCOQAET-GBTGNHPCSA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[2-hydroxy-2-(3-hydroxyphenyl)ethyl]-n-methylacetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1CC(=O)N(C)CC(O)C1=CC=CC(O)=C1 MQIBAVICCOQAET-GBTGNHPCSA-N 0.000 claims description 2
• JLGQTJOFCNKMEQ-IBVKSMDESA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-[4-(4-hydroxyphenyl)butyl]acetamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1CC(=O)NCCCCC1=CC=C(O)C=C1 JLGQTJOFCNKMEQ-IBVKSMDESA-N 0.000 claims description 2
• ZDIXLQJXKQNWEO-IBVKSMDESA-N 2-[3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]phenyl]-n-ethyl-n-[2-(4-hydroxyphenyl)ethyl]acetamide Chemical compound C=1C=CC(C[C@@H](C)NC[C@H](O)C=2C=NC(N)=CC=2)=CC=1CC(=O)N(CC)CCC1=CC=C(O)C=C1 ZDIXLQJXKQNWEO-IBVKSMDESA-N 0.000 claims description 2
• YSMQNXNKVKMIEO-QFIPXVFZSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-(2-chloro-4-hydroxyphenyl)acetamide Chemical compound C([C@H](O)C=1C=NC(N)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1CC(=O)NC1=CC=C(O)C=C1Cl YSMQNXNKVKMIEO-QFIPXVFZSA-N 0.000 claims description 2
• UGOVZVKGYPLUHL-QHCPKHFHSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-(2-hydroxy-5-methylphenyl)acetamide Chemical compound CC1=CC=C(O)C(NC(=O)CC=2C=C(CC(C)(C)NC[C@H](O)C=3C=NC(N)=CC=3)C=CC=2)=C1 UGOVZVKGYPLUHL-QHCPKHFHSA-N 0.000 claims description 2
• HBVGZGDXVFDMMT-QFIPXVFZSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-(3-hydroxy-4-methoxyphenyl)acetamide Chemical compound C1=C(O)C(OC)=CC=C1NC(=O)CC1=CC=CC(CC(C)(C)NC[C@H](O)C=2C=NC(N)=CC=2)=C1 HBVGZGDXVFDMMT-QFIPXVFZSA-N 0.000 claims description 2
• GDMGRJIFDPWGIY-QHCPKHFHSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-(3-hydroxy-4-methylphenyl)acetamide Chemical compound C1=C(O)C(C)=CC=C1NC(=O)CC1=CC=CC(CC(C)(C)NC[C@H](O)C=2C=NC(N)=CC=2)=C1 GDMGRJIFDPWGIY-QHCPKHFHSA-N 0.000 claims description 2
• CLWHSZIEGPPJNF-QFIPXVFZSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-(3-hydroxyphenyl)acetamide Chemical compound C([C@H](O)C=1C=NC(N)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1CC(=O)NC1=CC=CC(O)=C1 CLWHSZIEGPPJNF-QFIPXVFZSA-N 0.000 claims description 2
• KQFXVXPYMVEIQG-VWLOTQADSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-(5-tert-butyl-2-hydroxyphenyl)acetamide Chemical compound C([C@H](O)C=1C=NC(N)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1CC(=O)NC1=CC(C(C)(C)C)=CC=C1O KQFXVXPYMVEIQG-VWLOTQADSA-N 0.000 claims description 2
• KYMUUNDNWSTEFU-DEOSSOPVSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-[2-(2-hydroxyphenyl)ethyl]acetamide Chemical compound C([C@H](O)C=1C=NC(N)=CC=1)NC(C)(C)CC(C=1)=CC=CC=1CC(=O)NCCC1=CC=CC=C1O KYMUUNDNWSTEFU-DEOSSOPVSA-N 0.000 claims description 2
• WEQZENBWJGNVDE-VWLOTQADSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-[2-(3-ethoxy-4-hydroxyphenyl)ethyl]acetamide Chemical compound C1=C(O)C(OCC)=CC(CCNC(=O)CC=2C=C(CC(C)(C)NC[C@H](O)C=3C=NC(N)=CC=3)C=CC=2)=C1 WEQZENBWJGNVDE-VWLOTQADSA-N 0.000 claims description 2
• PEKSPLVVZVXYLE-DEOSSOPVSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-[2-(4-hydroxy-3-methoxyphenyl)ethyl]acetamide Chemical compound C1=C(O)C(OC)=CC(CCNC(=O)CC=2C=C(CC(C)(C)NC[C@H](O)C=3C=NC(N)=CC=3)C=CC=2)=C1 PEKSPLVVZVXYLE-DEOSSOPVSA-N 0.000 claims description 2
• RJEOZSVBWMVGDN-DEOSSOPVSA-N 2-[3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]phenyl]-n-ethyl-n-(3-hydroxyphenyl)acetamide Chemical compound C1([C@@H](O)CNC(C)(C)CC=2C=CC=C(C=2)CC(=O)N(CC)C=2C=C(O)C=CC=2)=CC=C(N)N=C1 RJEOZSVBWMVGDN-DEOSSOPVSA-N 0.000 claims description 2
• 125000006290 2-hydroxybenzyl group Chemical group [H]OC1=C(C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 claims description 2
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• UVFVAKJMQXHLIL-ZHRRBRCNSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-(2-hydroxy-5-methylphenyl)benzamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1C(=O)NC1=CC(C)=CC=C1O UVFVAKJMQXHLIL-ZHRRBRCNSA-N 0.000 claims description 2
• QTINNCGAARTPJK-QRQCRPRQSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-(3-hydroxy-2-methylphenyl)benzamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1C(=O)NC1=CC=CC(O)=C1C QTINNCGAARTPJK-QRQCRPRQSA-N 0.000 claims description 2
• BXTQSBJWMMSWBU-VFNWGFHPSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-(3-hydroxy-4-methoxyphenyl)benzamide Chemical compound C1=C(O)C(OC)=CC=C1NC(=O)C1=CC=CC(C[C@@H](C)NC[C@H](O)C=2C=NC(N)=CC=2)=C1 BXTQSBJWMMSWBU-VFNWGFHPSA-N 0.000 claims description 2
• APPVRYWZAFXGQX-VFNWGFHPSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-(3-hydroxyphenyl)benzamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1C(=O)NC1=CC=CC(O)=C1 APPVRYWZAFXGQX-VFNWGFHPSA-N 0.000 claims description 2
• CPBMOWXLMAIYRD-VFNWGFHPSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-(4-hydroxyphenyl)benzamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1C(=O)NC1=CC=C(O)C=C1 CPBMOWXLMAIYRD-VFNWGFHPSA-N 0.000 claims description 2
• GEIDDDLGOYNGHJ-HXOBKFHXSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-[2-(2-hydroxyphenyl)ethyl]benzamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1C(=O)NCCC1=CC=CC=C1O GEIDDDLGOYNGHJ-HXOBKFHXSA-N 0.000 claims description 2
• KDBGZBPJZJSLSK-HXOBKFHXSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-[2-(3-hydroxyphenyl)ethyl]benzamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1C(=O)NCCC1=CC=CC(O)=C1 KDBGZBPJZJSLSK-HXOBKFHXSA-N 0.000 claims description 2
• JBTSTUYGGAJQOD-HXOBKFHXSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-[2-(4-hydroxyphenyl)ethyl]benzamide Chemical compound C([C@@H](C)NC[C@H](O)C=1C=NC(N)=CC=1)C(C=1)=CC=CC=1C(=O)NCCC1=CC=C(O)C=C1 JBTSTUYGGAJQOD-HXOBKFHXSA-N 0.000 claims description 2
• NLKDZJIWBSKQGE-CLOONOSVSA-N 3-[(2r)-2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]propyl]-n-ethyl-n-[2-(4-hydroxyphenyl)ethyl]benzamide Chemical compound C=1C=CC(C[C@@H](C)NC[C@H](O)C=2C=NC(N)=CC=2)=CC=1C(=O)N(CC)CCC1=CC=C(O)C=C1 NLKDZJIWBSKQGE-CLOONOSVSA-N 0.000 claims description 2
• YOVAQOWIQHPGMV-QFIPXVFZSA-N 3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]-n-(3-hydroxy-2-methylphenyl)benzamide Chemical compound CC1=C(O)C=CC=C1NC(=O)C1=CC=CC(CC(C)(C)NC[C@H](O)C=2C=NC(N)=CC=2)=C1 YOVAQOWIQHPGMV-QFIPXVFZSA-N 0.000 claims description 2
• IBZYJGDVZKUAIG-QFIPXVFZSA-N 3-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]-2-methylpropyl]-n-(3-hydroxy-4-methylphenyl)benzamide Chemical compound C1=C(O)C(C)=CC=C1NC(=O)C1=CC=CC(CC(C)(C)NC[C@H](O)C=2C=NC(N)=CC=2)=C1 IBZYJGDVZKUAIG-QFIPXVFZSA-N 0.000 claims description 2
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